Hydroxyphenylacetic acid → 3,3,3-Triphenylpropyl 2-(4-hydroxyphenyl)acetate

Participants

Reaction Steps

To triphenylpropanol (3.98 mmol), 4-hydroxyphenylacetic acid (3.98 mmol), and triphenylphosphine (4.39 mmol) in dry THF (20 mL) at 0° C. under a nitrogen atmosphere, was added DEAD (4.39 mmol) in dry THF (20 mL) over 15 minutes. The reaction was stirred at room temperature for 16 h and then the THF was evaporated. The residue was chromatographed on silica gel using 15-30% EtOAc/hexanes. White solid, mp=136°-138° C. (ether), 34% yield. 1H NMR δ 7.15-7.27 (m, 15H), 7.10 (d, J=8.5 Hz, 2H), 6.77 (d, J=8.5 Hz, 2H), 4.90 (s, 1H), 3.90 (t, J=7.9 Hz, 2H), 3.47 (s, 2H), 2.93 (t, J=7.9 Hz, 2H). Anal. calcd. for C29H26O3 : C, 82.44; H, 6.20. Found: C, 82.29; H, 6.24.

Provenance & Evidence